Tetrahedron Letters, Journal Year: 2024, Volume and Issue: 155, P. 155440 - 155440
Published: Dec. 27, 2024
Language: Английский
Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: 63(8)
Published: Jan. 8, 2024
A mild photoredox catalyzed construction of sulfides, disulfides, selenides, sulfoxides and sulfones from unstrained ketone precursors is introduced. Combination this deacylative process with S
Language: Английский
Citations
21
The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(8), P. 5783 - 5796
Published: April 9, 2024
A visible-light-induced radical-cascade selenocyanation/cyclization of N-alkyl-N-methacryloyl benzamides, 2-aryl-N-acryloyl indoles, and N-methacryloyl-2-phenylbenzimidazoles with potassium isoselenocyanate (KSeCN) was developed. The reactions were carried out inexpensive KSeCN as a selenocyanation reagent, persulfate an oxidant, 2,4,6-triphenylpyrylium tetrafluoroborate bifunctional catalyst for phase-transfer catalysis, photocatalysis. library selenocyanate-containing isoquinoline-1,3(2H,4H)-diones, indolo[2,1-a]isoquinoline-6(5H)-ones, benzimidazo[2,1-a]isoquinolin-6(5H)-ones achieved in moderate to excellent yields at room temperature under visible-light ambient conditions. Importantly, the present protocol features mild reaction conditions, large-scale synthesis, simple manipulation, product derivatization, good functional group, heterocycle tolerance.
Language: Английский
Citations
10
The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(6), P. 4120 - 4127
Published: March 5, 2024
Heteroatom-adjacent C(sp3) radical cyclization of N-arylacrylamides provides a straightforward pathway to synthesize valuable 3-functionalized oxindoles. Traditional reactions normally require harsh conditions or transition-metal catalysts. Here, we developed metal-free, diversity-oriented synthesis oxindoles via photochemically induced selective cleavage C(sp3)–H bonds. A variety 3-substituted with functionalities such as ethers, polyhalogens, benzyl, and formyl groups can be obtained by rational design. This strategy is characterized its simple operation mild conditions, aligning well the developmental requirements for sustainable chemistry. The gram-scale continuous-flow efficient construction bioactive molecules highlight practical utility.
Language: Английский
Citations
5
Tetrahedron, Journal Year: 2024, Volume and Issue: 160, P. 134050 - 134050
Published: May 25, 2024
Language: Английский
Citations
4
Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: unknown
Published: July 24, 2024
Abstract The homolysis of chemical bonds represents one the most fundamental reactivities excited molecules. Historically, it has been exploited to generate radicals under ultraviolet (UV) light irradiation. However, unlike contemporary radical‐generating mechanisms, direct excitation homolyze and produce aliphatic carbon‐centered visible remains rare, especially in metallaphotoredox cross couplings. Herein, we present our design dihydropyrimidoquinolinone (DHPQ) reagents derived from ketones, which can undergo formal deacylation homolytic C−C bond cleavage release alkyl without external photocatalysts. Spectroscopic computational analysis reveal unique optical structural features DHPQs, rationalizing their faster kinetics radical generation than a structurally similar but visible‐light transparent precursor. Such capability allows DHPQ facilitate wide range Ni‐metallaphotoredox couplings with aryl, alkynyl acyl halides. Other catalytic non‐catalyzed alkylative transformations DHPQs are also feasible various acceptors. We believe this work would be broad interest, aiding synthetic planning simplified operation expanding reach photocatalyst‐free approaches cutting‐edge research.
Language: Английский
Citations
4
Organic Letters, Journal Year: 2025, Volume and Issue: unknown
Published: Jan. 10, 2025
Herein, we report a formal C–C bond azidation and cyanation of unactivated aliphatic ketones using commercially available tosyl azide cyanide, respectively. A visible-light-mediated organophotocatalyst enables radical ketone-derived pro-aromatic dihydroquinazolinones (under mostly redox-neutral conditions) as supported by preliminary mechanistic studies. These metal-free scalable protocols can be used to synthesize tertiary, secondary, primary alkyl azides nitriles with good functional group tolerance postsynthetic diversification the group, including bioconjugation.
Language: Английский
Citations
0
Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(27), P. 5561 - 5568
Published: Jan. 1, 2024
An organo-photoredox catalyzed defluorinative alkylation of ketone-derived dihydroquinazolinones with α-trifluoromethyl alkenes is described, providing a facile access to diverse set gem -difluoroalkenes.
Language: Английский
Citations
3
The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(7), P. 5060 - 5068
Published: March 25, 2024
Radical cyclization has been demonstrated to be an efficient method access functionalized heterocycles from easily accessible raw materials. Described herein is the development of a photocatalytic proton-coupled electron transfer (PCET) strategy for synthesis isoquinoline-1,3-diones using readily prepared naphthalimide (NI)-based organic photocatalysts. The process features free metal-complex photocatalysts, acids, and mild reaction conditions. This radical protocol broad substrate scope can effectively applied variety medicinally relevant substrates. Furthermore, control experiments were conducted elucidate mechanism this visible light-induced methodology.
Language: Английский
Citations
2
Chinese Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 44(5), P. 1549 - 1549
Published: Jan. 1, 2024
The visible-light-induced C-C bond cleavage of dihydroquinazolinone to generate alkyl radicals for defluorinated alkylation reactions with α-trifluoromethyl alkene is reported.The method featured as transition-metal-free, mild conditions, base-or additive-free, and has a wide range substrate applicability, which provides convenient efficient new the synthesis various alkyl-substituted gem-difluoroalkene.
Language: Английский
Citations
2
Synlett, Journal Year: 2023, Volume and Issue: 35(10), P. 1072 - 1088
Published: Oct. 24, 2023
Abstract The recent prominence of ketones as handles for sp3-rich radicals has expanded the paradigm synthetic utility ketones, putting ubiquitous functional group once again into spotlight in years. One emerging strategy arose through ketone-derived pro-aromatic reagents form dihydrobenzothiazoline (BTZ), dihydroquinazolinone (DHQZ), dihydropyrazole (DHP), and dihydro-1,2,4-triazole (DHT) key intermediates aromaticity-promoted C–C bond homolytic fission. formed sp3-radicals could then participate various radical functionalizations, including alkylations, arylations, olefination, alkynylation, silylations, amination, thiolation, deuteration, among others, either photocatalytic, thermal, or oxidative conditions. In this review, we highlight implications advances using these transfer reactions deconstructive functionalization. 1 Introduction 2 Aromatization-Driven Bond Scission Ketones 3 Photochemical Reactions Ketone-Derived Pro-aromatic Reagents 4 Non-photochemical 5 Conclusion Future Outlook
Language: Английский
Citations
5